The only silly question is one you do not learn from... but these things you mentioned and light are unrelated so I'll just try to break them down briefly.
Gravity assist is simply using a large mass for its attractive force, in Newtonian physics, or "falling into" a gravity well in general relativity but this does not lead to an assist directly, since you have to "slingshot" around the mass and are pulled back by gravity slowing you back down or "climbing" back out of the well in GR. The gain in velocity is acquired while you are in "orbit" around the mass in which may be brief but effective in taking some of the orbital energy from a mass orbiting around another body (the opposite direction slows you down and gives the larger mass slightly more energy).
The Penrose process is different because it doesn't involve the mass orbiting anything, it involves a smaller mass orbiting a quickly rotating larger mass and the smaller mass can leave the system, perhaps broken and part falls in with other other part being ejected with more energy, but it actually slows down the rotation of the larger mass a bit. If it all falls in it adds its energy to the rotation.
As for photons at c? They are always at c! When we say c is the speed of light in a vacuum, that is its normal propagating velocity no matter who sees it at what speed they are moving in however much gravity. It only changes when it bounces off of something or it gets absorbed by an atom and a different photon may be emitted. What can change is its vector of travel, for example, gravitational lensing, or its frequency, which many factors can affect, but since you are interested in large masses I'll just touch on that. As a photon approaches a mass, it has to gain energy. Its velocity is stuck on max, but its energy can vary by wavelength, so to pass this energy to the photon the wavelength gets shorter... giving it a faster frequency. The opposite happens leaving a gravity well, causing it red shift to lower energy and slower frequency. I'm not sure if orbital or rotational energy affects it, but I'd bet it still goes c.